A-chloropropionate

Nitroethane may be similarly obtained from sodium a chloropropionate. This is a general reaction for a chloro carboxylic acids, but in practice only monochloroacetic acid and a chloropropionic acid are readily available. 

Benzoquinone a-Chloropropionic [Propanoic acid, 2-chloro ] 2-(a-Chloroethyl) [2,5-Cyclohexadiene-1,4-dione, 2-( 1 -chloroethyl) -] 45" 2... 

Laboratory synthesis yields a racemic mixture. When a compound containing an asymmetric carbon atom is synthesised in the laboratory from a compound that has none, the product is always a racemic mixture. Thus if a chloropropionic acid is prepared from propionic acid a racemic mixture results ... 

Alanine was prepared in i860 by Kolbe by the second general method, by the action of ammonia upon a-chloropropionic acid —... 

Some preliminary studies were conducted to determine whether one of two proposed reactions could account for the appearance of pyruvate from dalapon. The precursor of pyruvate in this system is probably the a-hydroxy-a-chloropropionate. This compound is unstable and will spontaneously give rise to pyruvic acid. The enzyme apparently forms a-chloro-a-hydroxypropionate from dalapon. One reaction system by which the enzyme could form a-chloro-a-hydroxypropionate from dalapon would involve a direct substitution reaction (Reaction 1). In this case there would be a direct nucleophilic attack at carbon-2, led by a hydroxyl group to form the desired product. 

The method has been used for the preparation of dihalides, e.g., 1,9-dichlorononane (93%) unsaturated halides, e.g., 11-undecylenyl chloride (83%) halo ethers, e.g., /3-ethoxyethyl chloride (80%) halo ketones, e.g., desyl chloride (79%) halo esters, e.g, methyl a-chloropropionate (71%) halo cyanides, e.g., phenylchloroacetonitrile (80%) and aminoalkyl halides,An interesting isomerisation has been observed in liberating 2-diethylamino-l-chloropropane from its hydrochloride salt l-diethylamino-2-chloropropane is formed. ... 

CH3—CO—CHCl—CH3 and CH3—CHCl—CO —OCgHj a chloroethyl methyl ketone and ethyl a chloropropionate... 

A highly asymmetric induction in the nickel-catalyzed electroreductive couplings of aryl halides with a-chloropropionic acid derivatives was reported by Nedelec and coworkers [Eq, (65)] [495]. 

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